Dissymmetric sulfoether is a kind of important sulfur-containing compounds. It is not only widely found in natural products, pharmaceutically active molecules, but also acts as advanced materials and metal ligands, or as important organic synthesis intermediates.
Dissymmetric sulfoether compounds have a wide range of applications in biomedicine, for example:
Methionine is one of the essential amino acids in the human body, and it participates in protein synthesis. Because it can not be generated by the body itself, it must be obtained from the outside. Lack of methionine will lead to inhibition of protein synthesis in vivo, causing damage to the body. At present, methionine is usually synthesized by the coupling reaction of halide and thiol and its related derivatives under the catalysis of transition metal.
Cilastatin is a thiamycin antibiotic with carbapenem ring, which is a commercially available antimicrobial agent prepared by semi-synthesis of thiamycin from culture medium of S. cattleya. Cilastatin is used for sepsis caused by sensitive organism, infective endocarditis, osteomyelitis, arthritis, skin and soft tissue infections. At present, Cilastatin is synthesized by direct addition of thiol and its related derivatives to unsaturated compounds under the condition with transition metal or no metal.
Cinanserin can be used to treat psychiatric disorders. At present, Cinanserin is usually synthesized by addition of thiol and its related derivatives to alkynes under the condition of transition metal catalyst.
It can be seen that thiol compounds, which are highly toxic, malodorous, sensitive and perishable, are inevitably used in the reaction process of the current method for synthesizing dissymmetric sulfoether in addition to the need for expensive metal catalyst and harsh reaction conditions (anhydrous, anaerobic, etc.). These shortcomings seriously restrict the practical use of the method. Therefore, the development of novel synthetic methods for dissymmetric sulfoether compounds has been a hot research field in organic chemistry and pharmaceutical chemistry.